Morpholine → HCID 68663195, compound

HRID 452728Notes

Reaction equation

HRID 452728 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]([OH:17])=O)[C:11]=3[CH:18]=2)=[N:4][N:3]=1.C(Cl)(=O)C(Cl)=O.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C(=O)([O-])O.[Na+]>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[O:17])[C:11]=3[CH:18]=2)=[N:4][N:3]=1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 68663145HCID 68663145, compound

Product 1

HCID 68663195HCID 68663195, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-carboxylic acid (97.7 mg, 0.400 mmol) and N,N-dimethylformamide (1 drop) in tetrahydrofuran (5 mL) was added oxalyl chloride (0.0698 mL, 0.800 mmol) at room temperature, and the resulting mixture was stirred for 15 min. The reaction mixture was added dropwise to a mixture of morpholine (0.105 mL, 1.20 mmol) and saturated aqueous sodium hydrogen carbonate solution (5 mL) at room temperature, and the resulting mixture was stirred for 1 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate), and recrystallized from methanol/water to give the title compound (33.8 mg, yield 27%) as colorless crystals.

Workup

  1. stirringthe resulting mixture was stirred for 1 hr
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (ethyl acetate)
  6. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-7abebec847b9462b935520785c260c13
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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